After 10 years on WHS V1, I decided to upgrade to Windows Server 2016 Essentials, and currently getting it set up.

The question I have is on how to setup the Anywhere access - specifically ports 80 and 443. The way I have it now, my router redirects port 80 to my WHS server, and I have 443 redirected to the CQC Web Server, mainly to run the Echo support.

I switched port 80 on my router to point to the WSE server, but not sure how to handle port 443. Should I go ahead and move the CQC Webserver to the WSE 2016 server? Can I move just the CQC Webserver to the WSE Server? Configuration wise, I would like to leave my CQC server as is, as it is in the wiring closet and attached to too many things.

Is there another way I could have the echo support and the WSE Anywhere access?

From a security standpoint, are their any issues with what I am attempting to do?

You can just install another instance of the web server on the new machine and point 443 at it (with the correct security token setup of course.) The WS can be installed on multiple CQC enabled machines. You can leave the original web server on the other machine in case of future need, or you can remove it if you don't want it there anymore taking up those ports.

If I wanted to keep CQC Webserver secure port separate from the MSE secure port, could I change the port setting in the installation to something different and still have the Echo integration and the new CQC WebRiva work? (assuming I specify the port on the calls to the CQC Echo / Webserver)

Yeh, you can set it to what you want, you just have to indicate the port in the URLs if you don't use the defaults. However, you can't have two security certificates for the same machine unless you are accessing the machine via two different domain/network names. The name of the machine is used to find the certificate, so there can only be one for a given machine name. So you'd sort of need to keep them on separate machines, or some more complex, multi-homed scheme or something.